Propylene glycol dinitrate
| Names | |
|---|---|
| IUPAC name
Propylene dinitrate
| |
| Other names
1-Nitrooxypropan-2-yl nitrate
1,2-Bis(nitrooxy)propane 1,2-Propanediol dinitrate 1,2-Propylene glycol dinitrate Isopropylene nitrate PGDN Propane-1,2-diyl dinitrate | |
| Properties | |
| C3H6N2O6 | |
| Molar mass | 166.089 g/mol |
| Appearance | Colorless liquid |
| Odor | Sweet, disagreeable |
| Density | 1.232 g/cm3 (at 20 °C) |
| Melting point | −27.7 °C (−17.9 °F; 245.5 K) |
| Boiling point | 121 °C (250 °F; 394 K) (decomposition begins below boiling point) |
| 0.797 g/100 ml (25 °C) | |
| Vapor pressure | 0.07 mmHg (22 °C) |
| Hazards | |
| Safety data sheet | None |
| Lethal dose or concentration (LD, LC): | |
| LD50 (Median dose)
|
930 mg/kg (rat, IP) |
| Related compounds | |
| Related compounds
|
Ethylene glycol dinitrate Nitroglycerin |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
Propylene glycol dinitrate (PGDN) is an organic chemical, an ester of nitric acid and propylene glycol. It is structurally similar to nitroglycerin except that it has one fewer nitrate group, or EGDN but with a methyl group.
Contents
Properties
Chemical
Propylene glycol dinitrate burns with a clean flame and if heated enough it may explode.
- C3H6(ONO2)2 → 3 CO + 3 H2O + N2
Physical
PGDN is a colorless liquid, with a disagreeable odor. It is immiscible with water, but much more soluble in other organic solvents.
Explosive
PGDN is shock and friction sensitive, albeit less so than nitroglycerine. It has a detonation velocity of 6900 m/s at a density of 1.37.[1]
Availability
Propylene glycol dinitrate is not available commercially and has to be prepared in situ.
Preparation
Propylene glycol dinitrate can be prepared by nitrating dry propylene glycol using concentrated nitric acid and sulfuric acid.[2]
Projects
- Smokeless powder
- Various propellants (Otto fuel II e.g.)
Handling
Safety
PGDN, like all nitrate esters, affects blood pressure, causes respiratory toxicity, damages liver and kidneys, distorts vision, causes methoglobinuria, and can cause headache and lack of coordination. It may be absorbed through skin. Its primary toxicity mechanism is methemoglobinemia. It may cause permanent nerve damage.
For occupational exposures, the National Institute for Occupational Safety and Health has set a recommended exposure limit at 0.05 ppm (0.3 mg/m3) over an eight-hour workday, for dermal exposures.
Storage
Should not be stored for long periods of time and used as soon as possible.
2-Nitrodiphenylamine or di-n-butyl sebacate are sometimes used as stabilizers.
Disposal
Can be diluted with a more flammable solvent and burned outside.
Alternatively it can be diluted in a solvent, then carefully poured in a cooled solution of NaOH to hydrolyze it.
References
- ↑ G. D. Kozak , "Measurement and calculation of the ideal detonation velocity for liquid nitrocompounds", Combustion, Explosion and Shock Waves, vol. 34, p. 581–586 (1998)
- ↑ E-Smoking Liquids as Precursors for Liquid Nitroesters, Hichem FETTAKA, Michel H. LEFEBVRE
